Novel organic compounds and organic electroluminescent device including the same

ABSTRACT

The present disclosure relates to a novel organic compound and an organic electroluminescent device including the same. More specifically, the present disclosure relates to a deuterated organic compound and an organic electroluminescent device including at least one organic layer made of the deuterated organic compound. Thus, the organic electroluminescent device exhibits a longer lifetime, lower voltage implementation, and improved luminous efficiency.

CROSS-REFERENCE TO RELATED APPLICATIONS

This application claims the priority of Korean Patent Application Nos.10-2018-0036167 filed on Mar. 28, 2018, and 10-2018-0099515 filed onAug. 24, 2018, in the Korean Intellectual Property Office, thedisclosure of which is hereby incorporated by reference in its entirety.

BACKGROUND Technical Field

The present disclosure relates to a novel organic compound and anorganic electroluminescent device including the same. More specifically,the present disclosure relates to a deuterated organic compound and anorganic electroluminescent device including at least one organic layermade of the deuterated organic compound.

Description of the Related Art

An organic electroluminescent device has a simpler structure than thoseof other flat panel display devices such as a liquid crystal display(LCD), a plasma display panel (PDP), and a field emission display (FED).The organic electroluminescent device has various advantages in amanufacturing process, has excellent luminance and viewing anglecharacteristics, and a high response speed and a low driving voltage.Thus, the organic electroluminescent device is being actively developedso as to be used for a flat panel display such as a wall-hanging TV oras a light source such as a backlight of a display, a illuminationdevice, and a billboard.

Generally, in the organic electroluminescent device, when a voltage isapplied thereto, holes injected from a anode and electrons injected froma cathode are recombined with each other to form excitons aselectron-hole pairs. Then, energy of the excitons is transmitted to alight emitting material to emit light beams.

C. W. Tang reported a low voltage-driven organic electroluminescentdevice including an organic thin film stack formed between two opposingelectrodes to improve efficiency and stability of the organicelectroluminescent device (C. W. Tang, S. A. Vanslyke, Applied PhysicsLetters, vol. 51, p. 913, 1987). Subsequently, researches on organicmaterials for the organic electroluminescent device having the organicthin film stack have been actively conducted.

Generally, the organic electroluminescent device has a structureincluding a cathode (electron injection electrode), a anode (holeinjection electrode), and at least one organic layer between the twoelectrodes.

Most of organic materials used in the organic electroluminescent deviceare pure organic materials or coordination complexes between organicmaterials and metals. The organic materials used in the organicelectroluminescent device may be classified into a hole-injectingmaterial, a hole-transporting material, a light-emitting material, anelectron-transporting material, and an electron-injecting material. Inthis connection, the hole-injecting materials or hole-transportingmaterials may mainly employ organic materials which are easily oxidizedand which are electrochemically stable in the oxidized state. Theelectron-injecting materials and electron-transporting materials maymainly employ organic materials that are easily reduced andelectrochemically stable in the reduced state.

The light-emitting layer material preferably employs a materialelectrochemically stable in both the oxidized and reduced states.Further, the light-emitting layer material preferably employs a materialhaving high efficiency of light emission in which excitons are appliedthereto to emit light beams. In the light-emitting layer made of thematerials having such properties, electrons recombines with holes tocreate an excited state. When the excited state returns to a groundstate, the light emission may occur. The compound type of each organiclayer ultimately affects characteristics and implementations of theorganic electroluminescent device.

Recently, the organic electroluminescent device requires a longerlifetime, lower voltage implementation, and improved luminousefficiency. Those requirements may lead to the lower power consumptionand improved durability of the device.

To this end, the present inventors attempted to achieve the low voltageimplementation and improved lifetime using deuterated anthracene organiccompounds including polar molecules.

PRIOR ART DOCUMENT

[Patent Literature] Korean Patent Application Publication No.10-2013-0010633; Korean Patent No. 10-1368164

BRIEF SUMMARY

One purpose of the present disclosure is to provide a novel compoundthat may be employed as a blue host material for a light-emitting layer.

Another purpose of the present disclosure is to provide an organicelectroluminescent device in which the device includes the novelcompound containing polar molecules to allow a driving voltage to belower and in which the device includes a deuterated anthracene organiccompound to realize the increased lifetime, and excellent luminescenceefficiency and external quantum efficiency (EQE) characteristics.

The purposes of the present disclosure are not limited to theabove-mentioned purposes. Other purposes and advantages of the presentdisclosure, as not mentioned above, may be understood from the followingdescriptions and more clearly understood from the embodiments of thepresent disclosure. Further, it will be readily appreciated that theobjects and advantages of the present disclosure may be realized byfeatures and combinations thereof as disclosed in the claims.

In a first aspect of the present disclosure, there is provided acompound represented by a following Chemical Formula 1:

wherein Y denotes a substituent represented by a following ChemicalFormula 2:

-   -   wherein X is O or S,    -   n is an integer of 0 to 4,    -   m is an integer of 0 to 3,

wherein L₁ and L₂ are the same or different from each other, and each ofL₁ and L₂ independently are selected from a group consisting of a directbond, a substituted or unsubstituted arylene group having 6 to 30 carbonatoms, a substituted or unsubstituted heteroarylene group having 6 to 30ring constituting atoms, a substituted or unsubstituted alkylene grouphaving 2 to 10 carbon atoms, a substituted or unsubstitutedcycloalkylene group having 2 to 10 carbon atoms, a substituted orunsubstituted alkenylene group having 2 to 10 carbon atoms, asubstituted or unsubstituted cycloalkenylene group having 2 to 10 carbonatoms, a substituted or unsubstituted heteroalkylene group having 2 to10 carbon atoms, a substituted or unsubstituted heterocycloalkylenegroup having 2 to 10 carbon atoms, a substituted or unsubstitutedheteroalkenylene group having 2 to 10 carbon atoms, and a substituted orunsubstituted heterocycloalkenylene group having 2 to 10 carbon atoms,

wherein Ar₁ is selected from a group consisting of a substituted orunsubstituted aryl group having 6 to 30 carbon atoms, a substituted orunsubstituted heteroaryl group having 3 to 30 carbon atoms, asubstituted or unsubstituted alkyl group having 1 to 20 carbon atoms, asubstituted or unsubstituted cycloalkyl group having 1 to 20 carbonatoms, a substituted or unsubstituted heteroalkyl group having 1 to 20carbon atoms, a substituted or unsubstituted heterocycloalkyl grouphaving 1 to 20 carbon atoms, a substituted or unsubstituted alkenylgroup having 1 to 20 carbon atoms, a substituted or unsubstitutedcycloalkenyl group having 1 to 20 carbon atoms, and a substituted orunsubstituted heteroalkenyl group having 1 to 20 carbon atoms,

wherein R₁, R₂, R₃, R₄, R₅, R₆, R₇, R₈, R₉, and R₁₀ are, at eachoccurrence, independently selected from a group consisting of hydrogen,deuterium, a substituted or unsubstituted alkyl group having 1 to 30carbon atoms, a substituted or unsubstituted cycloalkyl group having 3to 30 carbon atoms, a substituted or unsubstituted alkenyl group having2 to 30 carbon atoms, a substituted or unsubstituted alkynyl grouphaving 2 to 24 carbon atoms, a substituted or unsubstituted heteroalkylgroup having 2 to 30 carbon atoms, a substituted or unsubstitutedaralkyl group having 7 to 30 carbon atoms, a substituted orunsubstituted aryl group having 6 to 30 carbon atoms, a substituted orunsubstituted heteroaryl group having 2 to 30 carbon atoms, and asubstituted or unsubstituted heteroarylalkyl group having 3 to 30 carbonatoms, or wherein each occurrence of R₉ may, together with the carbon towhich it is attached, join with an adjacent R₉ to form a ring, orwherein each occurrence of R₁₀ may, together with the carbon to which itis attached, join with an adjacent R₁₀ to form a ring,

wherein each of R₁, R₂, R₃, R₄, R₅, R₆, R₇, R₈, R₉, R₁₀, L₁, L₂, and Ar₁is independently substituted with at least one substituent selected froma group consisting of hydrogen, deuterium, a cyano group, a nitro group,a halogen group, a hydroxy group, a substituted or unsubstituted alkylhaving 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkylgroup having 3 to 30 carbon atoms, a substituted or unsubstitutedalkenyl group having 2 to 30 carbon atoms, a substituted orunsubstituted alkynyl group having 2 to 24 carbon atoms, a substitutedor unsubstituted heteroalkyl group having 2 to 30 carbon atoms, asubstituted or unsubstituted aralkyl group having 7 to 30 carbon atoms,a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, asubstituted or a heteroaryl group having 2 to 30 carbon atoms, asubstituted or unsubstituted heteroarylalkyl group having 3 to 30 carbonatoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbonatoms, a substituted or unsubstituted alkylamino group having 1 to 30carbon atoms, a substituted or unsubstituted arylamino group having 6 to30 carbon atoms, a substituted or unsubstituted aralkylamino grouphaving 6 to 30 carbon atoms, a substituted or unsubstitutedheteroarylamino group having 2 to 24 carbon atoms, a substituted orunsubstituted alkylsilyl group having 1 to 30 carbon atoms, asubstituted or unsubstituted arylsilyl group having 6 to 30 carbonatoms, and a substituted or unsubstituted aryloxy group having 6 to 30carbon atoms, and

wherein at least one of substituents of L₁, L₂, Ar₁, R₁, R₂, R₃, R₄, R₅,R₆, R₇, R₈, R₉, or R₁₀ includes deuterium.

Further, according to the present disclosure, at least one of R₁, R₂,R₃, R₄, R₅, R₆, R₇, or R₈ preferably includes deuterium.

Furthermore, according to the present disclosure, L₁ preferably is oneselected from a group consisting of a direct bond, a substituted orunsubstituted arylene group having 6 to 30 carbon atoms, and asubstituted or unsubstituted heteroarylene group having 6 to 30 ringconstituting atoms. L₂ preferably is a direct bond or substituted orunsubstituted phenylene group. More preferably, L₁ is a direct bond or asubstituted or unsubstituted arylene group having 6 to 30 carbon atoms.

According to one preferred implementation of the present disclosure,there is provided an organic electroluminescent device including a firstelectrode; a second electrode facing away the first electrode; and atleast one organic layer interposed between the first electrode and thesecond electrode, wherein the at least one organic layer contains one ormore compounds of the Chemical Formula 1.

Further, the organic layer according to the present disclosure definesone selected from a group consisting of a hole-injecting layer, ahole-transporting layer, an electron-blocking layer, a light-emittinglayer, a hole-blocking layer, an electron-transporting layer and anelectron-injecting layer.

Furthermore, the organic layer in accordance with the present disclosuredefines a light-emitting layer, wherein the light-emitting layercontains a compound of the Chemical Formula 1 as a host material.

The organic electroluminescent device may include a vertical stack of aanode, a hole-injecting layer HIL), a hole-transporting layer HTL), alight-emitting layer EML), an electron-transporting layer ETL) and anelectron-injecting layer EIL) in this order. The device may furtherinclude an electron-blocking layer (EBL) and a hole-blocking layer (HBL)to enhance the light-emitting efficiency of the light-emitting layer,wherein the electron-blocking layer (EBL) and hole-blocking layer (HBL)sandwich the light-emitting layer (EML) therebetween.

Specifically, the organic electroluminescent device may further includean additional organic layer between the first electrode and thelight-emitting layer or between the light-emitting layer and the secondelectrode, wherein the additional organic layer defines at least oneselected from a group consisting of a hole-injecting layer, ahole-transporting layer, an electron-blocking layer, a light-emittinglayer, a hole-blocking layer, an electron-transporting layer and anelectron-injecting layer.

Further, when the device is embodied as a tandem organicelectroluminescent device, a single light emission unit may be composedof a stack of at least two light emission layers and a charge generationlayer (CGL) therebetween. The organic electroluminescent device mayinclude two or more stacks on a substrate, wherein each stack include avertical stack of a first electrode and a second electrode facing awayeach other, and a light-emitting layer disposed between the first andsecond electrodes to emit a specific light beam. The light-emittinglayer coupled to a charge-generating layer (CGL) composed of an N-typecharge-generating layer and a P-type charge-generating layer may renderblue, yellow or green or red.

In one implementation of the present disclosure, there is provide anorganic electroluminescent device including a first light emissionsub-stack for rendering first color light, and a second light emissionsub-stack stacked on the first light emission sub-stack for renderingsecond color light, wherein at least one of the first light emissionsub-stack and the second light emission sub-stack contains a hostmaterial, wherein the host material includes a compound represented by afollowing Chemical Formula 1:

wherein Y denotes a substituent represented by a following ChemicalFormula 2:

-   -   wherein X is O or S,    -   n is an integer of 0 to 4,    -   m is an integer of 0 to 3,

wherein L₁ and L₂ are the same or different from each other, and each ofL₁ and L₂ independently are selected from a group consisting of a directbond, a substituted or unsubstituted arylene group having 6 to 30 carbonatoms, a substituted or unsubstituted heteroarylene group having 6 to 30ring constituting atoms, a substituted or unsubstituted alkylene grouphaving 2 to 10 carbon atoms, a substituted or unsubstitutedcycloalkylene group having 2 to 10 carbon atoms, a substituted orunsubstituted alkenylene group having 2 to 10 carbon atoms, asubstituted or unsubstituted cycloalkenylene group having 2 to 10 carbonatoms, a substituted or unsubstituted heteroalkylene group having 2 to10 carbon atoms, a substituted or unsubstituted heterocycloalkylenegroup having 2 to 10 carbon atoms, a substituted or unsubstitutedheteroalkenylene group having 2 to 10 carbon atoms, and a substituted orunsubstituted heterocycloalkenylene group having 2 to 10 carbon atoms,

wherein Ar₁ is one selected from a group consisting of a substituted orunsubstituted aryl group having 6 to 30 carbon atoms, a substituted orunsubstituted heteroaryl group having 3 to 30 carbon atoms, asubstituted or unsubstituted alkyl group having 1 to 20 carbon atoms, asubstituted or unsubstituted cycloalkyl group having 1 to 20 carbonatoms, a substituted or unsubstituted heteroalkyl group having 1 to 20carbon atoms, a substituted or unsubstituted heterocycloalkyl grouphaving 1 to 20 carbon atoms, a substituted or unsubstituted alkenylgroup having 1 to 20 carbon atoms, a substituted or unsubstitutedcycloalkenyl group having 1 to 20 carbon atoms, and a substituted orunsubstituted heteroalkenyl group having 1 to 20 carbon atoms,

wherein R₁, R₂, R₃, R₄, R₅, R₆, R₇, R₈, R₉, and R₁₀ are, at eachoccurrence, independently selected from a group consisting of hydrogen,deuterium, a substituted or unsubstituted alkyl group having 1 to 30carbon atoms, a substituted or unsubstituted cycloalkyl group having 3to 30 carbon atoms, a substituted or unsubstituted alkenyl group having2 to 30 carbon atoms, a substituted or unsubstituted alkynyl grouphaving 2 to 24 carbon atoms, a substituted or unsubstituted heteroalkylgroup having 2 to 30 carbon atoms, a substituted or unsubstitutedaralkyl group having 7 to 30 carbon atoms, a substituted orunsubstituted aryl group having 6 to 30 carbon atoms, a substituted orunsubstituted heteroaryl group having 2 to 30 carbon atoms, and asubstituted or unsubstituted heteroarylalkyl group having 3 to 30 carbonatoms, or wherein each occurrence of R₉ may, together with the carbon towhich it is attached, join with an adjacent R₉ to form a ring, orwherein each occurrence of R₁₀ may, together with the carbon to which itis attached, join with an adjacent R₁₀ to form a ring,

wherein each of R₁, R₂, R₃, R₄, R₅, R₆, R₇, R₈, R₉, R₁₀, L₁, L₂, and Ar₁is independently substituted with at least one substituent selected froma group consisting of hydrogen, deuterium, a cyano group, a nitro group,a halogen group, a hydroxy group, a substituted or unsubstituted alkylhaving 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkylgroup having 3 to 30 carbon atoms, a substituted or unsubstitutedalkenyl group having 2 to 30 carbon atoms, a substituted orunsubstituted alkynyl group having 2 to 24 carbon atoms, a substitutedor unsubstituted heteroalkyl group having 2 to 30 carbon atoms, asubstituted or unsubstituted aralkyl group having 7 to 30 carbon atoms,a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, asubstituted or a heteroaryl group having 2 to 30 carbon atoms, asubstituted or unsubstituted heteroarylalkyl group having 3 to 30 carbonatoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbonatoms, a substituted or unsubstituted alkylamino group having 1 to 30carbon atoms, a substituted or unsubstituted arylamino group having 6 to30 carbon atoms, a substituted or unsubstituted aralkylamino grouphaving 6 to 30 carbon atoms, a substituted or unsubstitutedheteroarylamino group having 2 to 24 carbon atoms, a substituted orunsubstituted alkylsilyl group having 1 to 30 carbon atoms, asubstituted or unsubstituted arylsilyl group having 6 to 30 carbonatoms, and a substituted or unsubstituted aryloxy group having 6 to 30carbon atoms, and

wherein at least one of L₁, L₂, Ar₁, R₁, R₂, R₃, R₄, R₅, R₆, R₇, R₈, R₉,or R₁₀ includes deuterium.

Details of the compounds represented by the Chemical Formula 1 are asdescribed above.

In one implementation, the first light emission sub-stack includes avertical stack of a first electrode, a first hole-transporting layer, afirst light-emitting layer, and a first electron-transporting layer inthis order. The second light emission sub-stack includes a verticalstack of a second hole-transporting layer, a second light-emitting layerand a second electron-transporting layer in this order. At least one ofthe first light-emitting layer and the second light-emitting layer maycontain the host material.

FIG. 1 is a schematic cross-sectional view of a tandem organicelectroluminescent device having two light emission sub-stacks accordingto an exemplary first embodiment of the present disclosure. As shown inFIG. 1, the organic electroluminescent device 100 according to the firstembodiment of the present disclosure has a first electrode 110 and asecond electrode 120 facing away each other, and an organiclight-emitting stack 130 positioned between the first electrode 110 andthe second electrode 120. The organic light-emitting stack 130 includesa first light emission sub-stack (ST1) 140 located between the firstelectrode 110 and the second electrode 120 and containing a firstlight-emitting layer 144; a second light emission sub-stack (ST2) 150located between the first light emission sub-stack 140 and the secondelectrode 120 and containing a second light-emitting layer 154; and acharge-generating layer (CGL) 160 disposed between the first and secondlight emission sub-stacks 140 and 150.

The first electrode 120 acts as an anode for injecting holes. The firstelectrode 120 may be made of a conductive material with a high workfunction, for example, indium-tin-oxide (ITO), indium-zinc-oxide (IZO),and zinc-oxide (ZnO). The second electrode 120 acts as a cathode forinjecting electrons. The second electrode 120 may be made of aconductive material having a low work function, for example, aluminum(Al), magnesium (Mg), and aluminum-magnesium alloy (AlMg).

The first light emission sub-stack 140 includes a vertical stack of ahole-injecting layer 141 located between the first electrode 110 andfirst light-emitting layer 144, a first hole-transporting layer 142located between the hole-injecting layer 141 and the firstlight-emitting layer 144, and a first electron-transporting layer 146located between first light-emitting layer 144 and charge-generatinglayer 160.

The hole-injecting layer 141 improves properties of an interface betweenthe inorganic first electrode 120 and the first hole-transporting layer142 as an organic layer. The hole-injecting layer 141 may contain acompound represented by the Chemical Formula 1 described above. In oneexample, the hole-injecting layer 141 may contain at least one selectedfrom a group consisting of4,4′,4″-tris(3-methylphenylphenylamino)triphenylamine (MTDATA), copperphthalocyanine (CuPc), Tris(4-carbazoyl-9-yl-phenyl)amine (TCTA),N,N′-diphenyl-N,N′-bis(1-naphthyl)-1,1′-biphenyl-4,4″-diamine (NPB;NPD), 1,4,5,8,9,11-hexaazatriphenylenehexacarbonitrile (HATCN),1,3,5-tris[4-(diphenylamino)phenyl]benzene (TDAPB),poly(3,4-ethylenedioxythiphene)polystyrene sulfonate (PEDOT/PSS),2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F4-TCNQ), and/orN-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine.

In one example, a thickness of the hole-injecting layer 141 may be in arange of 1 to 150 nm. When the thickness of the hole-injecting layer 141is greater than or equal to 1 nm, the hole injection characteristics maybe improved. When the thickness is 150 nm or smaller, a problem of anincrease in the driving voltage due to an increase in the thickness ofthe hole-injecting layer 141 may be prevented. The hole-injecting layer141 may be omitted depending on a structure and properties of theorganic electroluminescent device.

The first hole-transporting layer 142 is located between thehole-injecting layer 141 and the first light-emitting layer 144. Thefirst light-emitting layer 144 is located between the firsthole-transporting layer 142 and the first electron-transporting layer146. The first electron-transporting layer 146 is located between thefirst light-emitting layer 144 and the charge-generating layer 160.

The second light emission sub-stack 150 includes a vertical stack of asecond hole-transporting layer 152, a second light-emitting layer 154, asecond electron-transporting layer 156, and an electron-injecting layer158 in this order. The second hole-transporting layer 152 is locatedbetween the charge-generating layer 160 and the second light-emittinglayer 154. The second light-emitting layer 154 is located between thesecond hole-transporting layer 152 and the second electrode 120.Further, the second electron-transporting layer 156 is located betweenthe second light-emitting layer 154 and the second electrode 120. Theelectron-injecting layer 158 is located between the secondelectron-transporting layer 156 and the second electrode 120.

Each of the first and second hole-transporting layers 142 and 152 maycontain a compound represented by the Chemical Formula 1 as describedabove. In one example, Each of the first and second hole-transportinglayers 142 and 152 may contain at least one selected from a groupconsisting ofN,N′-diphenyl-N,N′-bis(3-methylphenyl)-1,1′-biphenyl-4,4′-diamine (TPD),NPD, MTDATA, 1,3-bis(N-carbazolyl)benzene (mCP), CuPC, TCTA,tris(trifluorovinyl ether)-tris(4-carbazoyl-9-yl-phenyl)amine(TFV-TCTA), tris[4-(diethylamino)phenyl]amine,N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluorene-2-amine,tri-p-tolylamine,N-[1,1′-biphenyl]-4-yl-9,9-diMethyl-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]-amine),4,4′-bis(N-carbazolyl)-1,1′-biphenyl; CBP) and/or1,1-bis(4-(N,N′-di(ptolyl)amino)phenyl)cyclohexane (TAPC).

Each of the first hole-transporting layer 142 and the secondhole-transporting layer 152 may have a thickness of 1 to 150 nm. In thisconnection, when the thickness of each of the first and secondhole-transporting layers 142 and 152 is 1 nm or greater, the holetransporting property may be improved. When the thickness is 150 nm orsmaller, the problem of the increase in a driving voltage due to anincrease in the thickness of each of the first and secondhole-transporting layers 142 and 152 may be prevented. The firsthole-transporting layer 142 and the second hole-transporting layer 152may be made of the same material or may be made of different materials.

In one exemplary embodiment, each of the first and second light-emittinglayers 144, 154 may contain a host and dopants doped into the host. Thefirst and second light-emitting layers 144, 154 may render differentcolors. The dopant material may be added in a content of about 1 to 30%by weight based on a weight of the host material.

In one example, the first light-emitting layer 144 may render blue (B),red (R), green (G) or yellow (Y). When the first light-emitting layer144 renders blue (B), the layer 144 includes one of a bluelight-emitting material layer or a dark blue light-emitting materiallayer or sky blue light-emitting material layer. Alternatively, when thefirst light-emitting layer 144 may be composed of a combination (BR) ofa blue light-emitting material layer and a red light-emitting materiallayer, a combination (BYG) of a blue light-emitting material layer and ayellow-green (YG) light-emitting material layer, or a combination (BG)of a blue light-emitting material layer and a green light-emittingmaterial layer.

In one example, the second light-emitting layer 154 may render red (R),green (G), blue (B), or yellow green (YG). In one exemplary embodiment,the first light-emitting layer 144 may render blue, while the secondlight-emitting layer 154 may render green (G), yellow-green (YG), yellow(Y) or orange (0) having a longer wavelength than blue.

In one example, when the first light-emitting layer 144 emits bluelight, the first light-emitting layer 134 may contain at least onefluorescent host material selected from a group consisting of anthraceneand its derivatives, pyrene and its derivatives, and the compoundrepresented by the Chemical Formula 1, and fluorescence dopants dopedinto the host material.

In one example, the blue light-emitting host material employed for thefirst light-emitting layer 144 may include at least one selected from agroup consisting of 4,4′-bis(2,2′-diphenylyinyl)-1,1′-biphenyl (DPVBi),9,10-di-(2-naphtyl)anthracene (ADN), 2,5,8,11-(tetra-t-butylperylene(TBADN), 2-tert-butyl-9,10-di(2-naphthyl)anthracene,2-methyl-9,10-di(2-naphtyl)anthracene (MADN), and/or2,2′,2″-(1,3,5-benzinetriyl)-tris(1-phenyl-1-H-benzimidazole (TBPi).

Details of the compounds represented by the Chemical Formula 1 are asdescribed above.

Further, the blue light dopant material employed for the firstlight-emitting layer 144 may include at least one selected from a groupconsisting of 4,4′-bis(9-ethyl-3-carbazovinylene)-1,1′-biphenyl (BCzVBi)and/or diphenyl-[4-(2-[1,1;4,1]terphenyl-4-yl-vinyl)-phenyl]-amine(BD-1), spiro-DPVBi, spiro-CBP, distyrylbenzene (DSB) and itsderivatives, distyryl arylene (DSA) and its derivatives, polyfluoorene(PF)-based polymer, and polyphenylene vinylene (PPV)-based polymer.Alternatively, the blue dopant may include a phosphorescent dopant as aniridium-based dopant. In this connection, the first light-emitting layer144 may include a sky blue light-emitting material layer or a deep bluelight-emitting material layer. In this connection, an emissionwavelength from the first light emission sub-stack (144) may be in arange of 440 nm to 480 nm.

In one example, when the first light-emitting layer 144 is embodied as agreen (G) light-emitting material layer, the first light-emitting layer144 may include a phosphorescent light-emitting material layercontaining a host such as CBP and an iridium-based dopant (for example,dp2Ir (acac), op2Ir (acac)), or may contain the compound represented bythe Chemical Formula 1 as described above. However, the presentdisclosure is not limited thereto. Alternatively, the firstlight-emitting layer 144 may include a fluorescent light-emittingmaterial layer containing tris(8-hydroxyquinolinato)aluminum (Alq). Inthis connection, the emission wavelength from the first light-emittinglayer 144 may range from 510 nm to 570 nm.

Further, when the first light-emitting layer 144 is embodied as a red(R) light-emitting material layer, the first light-emitting layer 144may include a phosphorescent light-emitting material layer containing ahost material such as CBP, the compound represented by the ChemicalFormula 1 as described above, and at least one dopant selected from agroup consisting of bis(1-phenylisoquinoline)acetylacetonate iridium(PIQIr(acac)), bis((1-phenylquinoline)acetylacetonate iridium(PQIr(acac)), and octaethylporphyrin platinum (PtOEP). However, thepresent disclosure is not limited thereto.

Alternatively, the first light-emitting layer 144 may include afluorescent light-emitting material layer that contains1,3,4-oxadiazole:Tris(dibenzoylmethane)mono(1,10-phentathroline)europium(III)(PBD:Eu(DBM)3(Phen)) or perylene and its derivatives. In thisconnection, the emission wavelength from the first light-emitting layer144 may range from 600 nm to 650 nm.

Alternatively, when the first light-emitting layer 144 is embodied as ayellow (Y) light-emitting material layer, the first light-emitting layer144 may be composed of a single yellow-green (YG) light-emittingmaterial layer or a double layer of a YG light-emitting material layerand green (G) light-emitting material layer. In one example, when thefirst light-emitting layer 144 is embodied as the single yellowlight-emitting material layer, the yellow light-emitting material layermay contain a host material selected from a group consisting of CBP,bis(2-methyl-8-quinolinolate)-4-(phenylphenolato)aluminium (BAlq), andthe compound represented by the Chemical Formula 1 as described above,and a yellow-green phosphorescent dopant that emits yellow-green light.In this connection, the emission wavelength from the firstlight-emitting layer 144 may range from 510 nm to 590 nm.

In an alternative embodiment, in order to improve the red emissionefficiency of the light emitting diode 100 having a tandem structure,the first light-emitting layer 144 may be embodied as a combination oftwo light-emitting material layers, for example, a combination of ayellow-green light-emitting material layer and a red light emissionmaterial layer, or a combination of a blue light-emitting material layerand a red light-emitting material layer.

In one example, when the second light-emitting layer 154 is embodied asa yellow-green light-emitting material layer, the second light-emittinglayer 154 may be composed of a single yellow-green (YG) light-emittingmaterial layer or a combination of a yellow-green light-emittingmaterial layer and a green (G) light-emitting material layer. When theemitting layer 154 is composed of a single layer structure of ayellow-green light-emitting material layer, the second light-emittinglayer 154 may contain a host material selected from a group consistingof CBP, BAlq, and the compound represented by the Chemical Formula 1 asdescribed above, and a yellow-green phosphorescent dopant that emitsyellow-green. However, the present disclosure is not limited thereto.

Alternatively, when the second light-emitting layer 154 is embodied as ayellow light-emitting material layer, the second light-emitting layer154 may contain a host material selected from a group consisting of CBP,BAlq, and the compound represented by the Chemical Formula 1 asdescribed above, and a phosphorescent dopant that emits yellow. However,the present disclosure is not limited thereto.

In one implementation according to the present disclosure, at least oneof the first light-emitting layer and the second light-emitting layermay contain a host material including the compound of the chemicalformula 1 as described above.

In one example, the first electron-transporting layer 146 and the secondelectron-transporting layer 156 facilitate electrons transport in thefirst light emission sub-stack 140 and the second light emissionsub-stack 150, respectively. Each of the first and secondelectron-transporting layers 146 and 156 may contain one selected from agroup consisting of oxadiazole, triazole, phenanthroline, benzoxazole,benzothiazole, benzimidazole, triazine and derivatives thereof.

In one example, each of the first and second electron-transportinglayers 146 and 156 may contain at least one selected from a groupconsisting of Alq3, 2-biphenyl-4-yl-5-(4-tbutylphenyl)-1,3,4-oxadiazole(PBD), spiro-PBD, lithiumquinolate (Liq),2-[4-(9,10-Di-2-naphthalenyl-2-anthracenyl)phenyl]-1-phenyl-1Hbenzimidazol,3-(biphenyl-4-yl)-5-(4-tertbutylphenyl)-4-phenyl-4H-1,2,4-triazole(TAZ), 4,7-diphenyl-1,10-phenanthroline (Bphen), tris(phenylquinoxaline)(TPQ), 1,3,5-Tri[(3-pyridyl)-phen-3-yl]benzene (TmPyPB) and/or1,3,5-tris(N-phenylbenzimiazole-2-yl)benzene (TPBI).

Alternatively, each of the first and second electron-transporting layers146 and 156 may contain the compound represented by the Chemical Formula1 as described above.

Alternatively, each of the first and second electron-transporting layers146 and 156 may be doped with an alkali metal or an alkaline earth metalcompound. The metal components that may be employed as the dopants foreach of the first and second electron-transporting layers 146 and 156may include alkali metals such as lithium (Li), sodium (Na), potassium(K), and cesium (Cs), and/or alkaline earth metals such as magnesium(Mg), strontium (Sr), barium (Ba), and radium (Ra). However, the presentdisclosure is not limited thereto. The alkali metal or alkaline earthmetal compound may be added in a ratio of approximately 1 to 20% byweight. The present disclosure is not limited thereto.

Each of the first and second electron-transporting layers 146 and 156may have a thickness of 1 to 150 nm. When the thickness of each of thefirst and second electron-transporting layers 146 and 156 is 1 nm orgreater, this may prevent the electrons transporting property from beingdegraded. When the thickness of each of the first and secondelectron-transporting layers 146 and 156 is 150 nm or smaller, this mayprevent a driving voltage rise due to an increase in the thickness ofeach of the first and second electron-transporting layers 146 and 156.The first and second electron-transporting layers 146 and 156 may be ofthe same material or of different materials.

The electron-injecting layer 158 serves to facilitate the injection ofthe electrons. The electron-injecting layer 158 may contain alkalihalide-based materials such as LiF, NaF, KF, RbF, CsF, FrF, BeF₂, MgF₂,CaF₂, SrF₂, BaF₂ and RaF₂ and/or organic materials such as Liq (lithiumquinolate), lithium benzoate, sodium stearate, Alq3, BAlq, PBD,spiro-PBD, and TAZ. Alternatively, the electron-injecting layer 158 maycontain the compound represented by the Chemical Formula 1 as describedabove.

A thickness of the electron-injecting layer 158 may be in a range of 0.5to 50 nm. When the electron-injecting layer 158 is 0.5 nm or largerthick, this may prevent electrons injection characteristics from beingdegraded. When the thickness of the electron-injecting layer 158 is 50nm or smaller, this may prevent the driving voltage from rising due toan increase in the thickness of the electron-injecting layer 158.

According to an exemplary embodiment of the present disclosure, in theorganic electroluminescent device 100 having a tandem structure, thecharge-generating layer (CGL) 160 to increase current efficiency in eachlight-emitting layer and to distribute the charge smoothly may bedisposed between the first light emission sub-stack 140 and the secondlight emission sub-stack 150. That is, the charge-generating layer 160is located between the first light emission sub-stack 140 and the secondlight emission sub-stack 150, and the first light emission sub-stack 140and the second light emission sub-stack 150 are connected with eachother via the charge-generating layer 160. The charge-generating layer160 may be embodied as a PN-junction charge-generating layer composed ofa vertical stack of a N-type charge-generating layer 162 and the P-typecharge-generating layer 164.

The N-type charge-generating layer 162 is located between the firstelectron-transporting layer 146 and the second hole-transporting layer152. The P-type charge-generating layer 164 is located between theN-type charge-generating layer 162 and the second hole-transportinglayer 152. The charge-generating layer 160 generates charges and dividescharges into holes and electrons to provide electrons and holes to thefirst and second light emission sub-stacks 140 and 150 respectively.

That is, the N-type charge-generating layer 162 supplies electrons tothe first electron-transporting layer 146 of the first light emissionsub-stack 140. Then, the first electron-transporting layer 146 supplieselectrons to the first light-emitting layer 144 adjacent the firstelectrode 110. Meanwhile, the P-type charge-generating layer 164supplies holes to the second hole-transporting layer 152 of the secondlight emission sub-stack 150. Then, the second hole-transporting layer152 supplies holes to the second light-emitting layer 154 adjacent tothe second electrode 120.

In this connection, the P-type charge-generating layer 164 may be madeof a metal or an organic host material doped with a P-type dopant. Inthis connection, the metal may include one selected from a groupconsisting of Al, Cu, Fe, Pb, Zn, Au, Pt, W, In, Mo, Ni and Ti andalloys of at least two thereof. Further, the P-type dopant and the hostmaterial may employ materials known well to the skilled person to theart. In one example, the P-type dopant may include one selected from agroup consisting of F4-TCNQ, iodine, FeCl₃, FeF₃ and SbCl₅. Further, thehost material may include at least one selected from a group consistingof NPB, TPD, N, N, N′, N′-tetranaphthalenyl-benzidine (TNB) and HAT-CN.

Alternatively, the N-type charge-generating layer 162 may contain, as adopant, a metal compound such as an alkali metal or alkaline earth metalcompound. The alkali metal or alkaline earth metal may be added at aratio of about 1 to 30% by weight based on a weight of the organiccompound according to the present disclosure. However, the presentdisclosure is not limited thereto.

The N-type charge-generating layer 162 may be doped with an alkali metalor alkaline earth metal compound to improve electrons injection abilityinto the first electron-transporting layer 146. Specifically, when analkali metal or an alkaline earth metal is used as a dopant for theN-type charge-generating layer 162, the alkali metal or an alkalineearth metal used as the dopant bonds with the organic compound inaccordance with the present disclosure to form a gap state. Thus, adifference between energy levels of the N-type charge-generating layer162 and the P-type charge-generating layer 164 is reduced, and, thus,electrons injection ability from the N-type charge-generating layer 162to the first electron-transporting layer 146 is improved.

In FIG. 2, the organic electroluminescent device 200 includes a firstelectrode 210 and a second electrode 220 facing away each other, and anorganic light-emitting layer 230 positioned between the first electrode210 and the second electrode 220. The organic light-emitting layer 230may include a vertical stack of a first light emission sub-stack (ST1)240, a second light emission sub-stack (ST2) 250, a third light emissionsub-stack (ST3) 270, a first charge-generating layer (CGL1) 260, and asecond charge-generating layer (CGL2) 280. Alternatively, at least fourlight emission sub-stacks and at least three charge-generating layersmay be disposed between the first and second electrodes 210 and 220.

As described above, the first electrode 210 may act as an anode forinjecting holes, and may be made of any one of a conductive materialhaving a high work function, for example, ITO, IZO, or ZnO. The secondelectrode 220 may act as a cathode for injecting electrons and may bemade of any conductive material having a low work function, for example,aluminum (Al), magnesium (Mg), or aluminum-magnesium alloy (AlMg).

The first and second charge-generating layers 260 and 280 are locatedbetween the first and second light emission sub-stacks 240 and 250 andbetween the second and third light emission sub-stacks 250 and 270,respectively. The first light emission sub-stack 240, firstcharge-generating layer 260, second light emission sub-stack 250, secondcharge-generating layer 280 and third light emission sub-stack 270 aresequentially stacked on the first electrode 210. That is, the firstlight emission sub-stack 240 is positioned between the first electrode210 and the first charge-generating layer 260. The second light emissionsub-stack 250 is positioned between the first charge-generating layer260 and the second charge-generating layer 280. The third light emissionsub-stack 270 is located between the second electrode 220 and the secondcharge-generating layer 280.

The first light emission sub-stack 240 may include a vertical stack ofthe hole-injecting layer 241, the first hole-transporting layer 242, thefirst light-emitting layer 244, and the first electron-transportinglayer 246 on the first electrode 210. In this connection, thehole-injecting layer 241 and the first hole-transporting layer 242 arelocated between the first electrode 210 and the first light-emittinglayer 244. The hole-injecting layer 241 is located between the firstelectrode 210 and the first hole-transporting layer 242. Further, thefirst electron-transporting layer 246 is located between the firstlight-emitting layer 244 and the first charge-generating layer 260.

The hole-injecting layer 241, the first hole-transporting layer 242, thefirst light-emitting layer 244, and the first electron-transportinglayer 246 may be respectively identical with the hole-injecting layer141, the first hole-transporting layer 142, the first light-emittinglayer 144 and the first electron-transporting layer 146. Thus, adescription thereof will be omitted. For example, the firstlight-emitting layer 244 may be embodied as a blue (B) light-emittingmaterial layer. In this connection, the emission wavelength from thefirst light emission sub-stack 240 may range from 440 nm to 480 nm.

The second light emission sub-stack 250 may include a vertical stack ofthe second hole-transporting layer 252, the second light-emitting layer254, and the second electron-transporting layer 256. The secondhole-transporting layer 252 is located between the firstcharge-generating layer 260 and the second light-emitting layer 254. Thesecond electron-transporting layer 256 is located between the secondlight-emitting layer 254 and the second charge-generating layer 280.

The second hole-transporting layer 252, the second light-emitting layer254 and the second electron-transporting layer 256 may be respectivelyidentical with the second hole-transporting layer 152, the secondlight-emitting layer 154 and the second electron-transporting layer 156.Thus, a description thereof will be omitted. For example, the secondlight-emitting layer 254 may be embodied as a yellow-green (YG) oryellow (Y) light-emitting material layer. In this connection, theemission wavelength from the second light emission sub-stack 250 mayrange from 510 nm to 590 nm or range from 460 nm to 510 nm.

The third light emission sub-stack 270 may include a vertical stack of athird hole-transporting layer 272, a third light-emitting layer 274, athird electron-transporting layer 276, and an electron-injecting layer278. The third hole-transporting layer 272 is located between the secondcharge-generating layer 280 and the third light-emitting layer 274. Thethird electron-transporting layer 276 is located between the thirdlight-emitting layer 274 and the second electrode 220. Theelectron-injecting layer 278 is located between the thirdelectron-transporting layer 276 and the second electrode 220.

The third hole-transporting layer 272, the third electron-transportinglayer 276, and the electron-injecting layer 278 may be respectivelyidentical with the second hole-transporting layer 152, the secondelectron-transporting layer 156, and the electron-injecting layer 158.Thus, a description thereof will be omitted. The third light-emittinglayer 274 may be identical with the first light-emitting layer 144 orthe second light-emitting layer 154. For example, the thirdlight-emitting layer 274 may be embodied as a blue (B) light-emittingmaterial layer. In this connection, the emission wavelength from thethird light emission sub-stack 270 may range from 440 nm to 480 nm. Inanother alternative embodiment, the third light-emitting layer 274 maybe embodied as a yellow-green (YG) or yellow (Y) light-emitting materiallayer. In this case, the emission wavelength from the third lightemission sub-stack 270 may range from 460 nm to 590 nm.

In one implementation according to the present disclosure, at least oneof the first light-emitting layer, the second light-emitting layer andthe third light-emitting layer contains, as the host material, thecompound having the chemical formula 1 as described above.

The first charge-generating layer 260 is located between the first lightemission sub-stack 240 and the second light emission sub-stack 250. Thesecond charge-generating layer 280 is located between the second lightemission sub-stack 250 and the third light emission sub-stack 270. Eachof the first and second charge-generating layers 260 and 280 mayembodied as a PN-junction charge-generating layer composed of a verticalstack of each of the N-type charge-generating layers 262 and 282 andeach of the P-type charge-generating layers 264 and 284.

In the first charge-generating layer 260, the N-type charge-generatinglayer 262 is located between the first electron-transporting layer 246and the second hole-transporting layer 252. The P-type charge-generatinglayer 264 is located between the N-type charge-generating layer 262 andthe second hole-transporting layer 252.

Further, in the second charge-generating layer 280, the N-typecharge-generating layer 282 is located between the secondelectron-transporting layer 256 and the third hole-transporting layer272. The P-type charge-generating layer 284 is located between theN-type charge-generating layer 282 and the third hole-transporting layer272.

Each of the first and second charge-generating layers 260 and 280generates charges and/or divides the charges into electrons and holes tosupply the electrons and holes into each of the first to third lightemission sub-stacks 240, 250 and 270.

That is, in the first charge-generating layer 260, the N-typecharge-generating layer 262 supplies electrons to the firstelectron-transporting layer 246 of the first light emission sub-stack250. The P-type charge-generating layer 264 supplies holes to the secondhole-transporting layer 252 of the second light emission sub-stack 250.

Further, in the second charge-generating layer 280, the N-typecharge-generating layer 282 supplies electrons to the secondelectron-transporting layer 256 of the second light emission sub-stack250. The P-type charge-generating layer 284 supplies holes to the thirdhole-transporting layer 272 of the third light emission sub-stack 270.

In this connection, each of the P-type charge-generating layers 262 and282P may be made of a metal or an organic host material doped with aP-type dopant. In this connection, the metal may include one or moreselected from a group consisting of Al, Cu, Fe, Pb, Zn, Au, Pt, W, In,Mo, Ni, Ti and alloys of at least two thereof. Further, the P-typedopant and the host material may include materials conventionallyemployed by the skilled person to the art. For example, the P-typedopant may include a material selected from a group consisting ofF4-TCNQ, iodine, FeCl₃, FeF₃ and SbCl₅. Further, the host material mayinclude at least one material selected from the group consisting of NPB,TPD, TNB and HAT-CN.

Alternatively, each of the N-type charge-generating layer 262, 282 maycontain, as a dopant, a metal compound including an alkali metal oralkaline earth metal.

For example, each of the N-type charge-generating layers 262 and 282 maycontain at least one material selected from a group consisting of LiQ,LiF, NaF, KF, RbF, CsF, FrF, BeF₂, MgF₂, CaF₂, SrF₂, BaF₂ and RaF₂ inaddition to the organic compound according to the present disclosure.However, the present disclosure is not limited thereto.

The n-type charge-generating layers 262 and 282 may be doped with ametal or an alkaline earth metal compound to improve electrons injectionability into the electron-transporting layers 246 and 256.

The organic electroluminescent device according to the presentdisclosure may be applied to an organic light emitting display deviceand an illumination device using an organic electroluminescent device.In one example, FIG. 3 is a schematic cross-sectional view of an organiclight emission display device according to an exemplary embodiment ofthe present disclosure.

As shown in FIG. 3, the organic light emission display device 300 mayinclude a substrate 301, an organic electroluminescent device 400, andan encapsulation film 390 covering the organic electroluminescent device400. On the substrate 301, a driving thin-film transistor Td as adriving element and an organic electroluminescent device 400 connectedto the driving thin-film transistor Td are disposed.

Although not shown, following components may be disposed on thesubstrate 301: a gate line and a data line defining a pixel region andintersecting each other; a power line extending parallel to and spacedfrom either the gate line or the data line; a switching thin-filmtransistor connected to the gate line and data line; and a storage(capacitor) connected to one electrode of the switching thin-filmtransistor and the power line.

The driving thin-film transistor Td is connected to the switchingthin-film transistor. The driving thin-film transistor Td includes asemiconductor layer 310, a gate electrode 330, a source electrode 352,and a drain electrode 354.

The semiconductor layer 310 is formed on the substrate 301 and is madeof an oxide semiconductor or polycrystalline silicon. When thesemiconductor layer 310 is made of an oxide semiconductor material, ascreening pattern (not shown) may not be formed beneath thesemiconductor layer 310. The screening pattern prevents light fromentering the semiconductor layer 310, thereby preventing thesemiconductor layer 301 from being deteriorated by light. Alternatively,the semiconductor layer 310 may be made of polycrystalline silicon. Inthis case, impurities may be doped into both edges of the semiconductorlayer 310.

On the semiconductor layer 310, a gate insulating film 320 made of aninsulating material may be formed over an entire surface of thesubstrate 301. The gate insulating film 320 may be made of an inorganicinsulating material such as silicon oxide or silicon nitride.

On the gate insulating film 320, the gate electrode 330 made of aconductive material such as metal is formed in a center region of thesemiconductor layer 310. The gate electrode 330 is connected to aswitching thin-film transistor.

On the gate electrode 330, an inter-layer insulating film 340 made of aninsulating material is formed over the entire surface of the substrate301. The inter-layer insulating film 3402 may be made of an inorganicinsulating material such as silicon oxide or silicon nitride, or anorganic insulating material such as benzocyclobutene or photo-acryl.

The inter-layer insulating film 340 has contact holes 342 and 344exposing both lateral portions of the semiconductor layer 310. Thecontact holes 342 and 344 are spaced apart from the gate electrode 330and disposed on both sides of the gate electrode 330 respectively.

On the inter-layer insulating film 340, the source electrode 352 anddrain electrode 354 made of a conductive material such as a metal aredisposed. The source electrode 352 and drain electrode 354 are disposedabout the gate electrode 330 and are spaced from each other. The sourceelectrode 352 and drain electrode 354 contacts both sides of thesemiconductor layer 310 via the contact holes 342 and 344, respectively.The source electrode 352 is connected to a power line (not shown).

The semiconductor layer 310, the gate electrode 330, the sourceelectrode 352, and the drain electrode 354 define the driving thin-filmtransistor Td. The driving thin-film transistor Td has a coplanarstructure in which the gate electrode 330, the source electrode 352, andthe drain electrode 354 are disposed in a coplanar manner on thesemiconductor layer 310.

Alternatively, the driving thin-film transistor Td may have an invertedstaggered structure in which the gate electrode is located below thesemiconductor layer, and the source electrode and the drain electrodeare located above the semiconductor layer. In this case, thesemiconductor layer may be made of amorphous silicon. In one example,the switching thin-film transistor (not shown) may have substantiallythe same structure as the driving thin-film transistor Td.

In one example, the organic light emission display device 300 mayinclude a color filter 360 that absorbs light generated from the organicelectroluminescent device 400. For example, the color filter 360 mayabsorb red (R), green (G), blue (B), and white (W) light. In this case,color filter patterns that absorb the red, green and blue light may bedisposed separately on a pixel basis. Each of these color filterpatterns may overlap with a corresponding organic light-emitting layer430 of the organic electroluminescent device 400 that emits light havinga corresponding wavelength. Adopting the color filter 360 may allow theorganic light emission display device 300 to render a full color range.

For example, when the organic light emission display device 300 is of abottom light emission type, the color filter 360, which absorbs light,may be located above the inter-layer insulating film 340 in a region ofthe organic electroluminescent device 400. In an alternative embodiment,when the organic light emission display device 300 is of a top lightemission type, the color filter may be located on top of the organicelectroluminescent device 400, i.e., on top of the second electrode 420.In one example, the color filter 360 may have a thickness of 2 to 5 μm.In this connection, the organic electroluminescent device 400 may beembodied as an organic electroluminescent device having a tandemstructure as shown in FIG. 1 and FIG. 2.

In one example, a protective layer 370 having a drain contact hole 372exposing the drain electrode 354 of the driving thin-film transistor Tdmay be formed to cover the driving thin-film transistor Td.

On the protective layer 370, the first electrode 410 connected to thedrain electrode 354 of the driving thin-film transistor Td via the draincontact hole 372 may be formed on a pixel region basis.

The first electrode 410 may act as an anode and may be made of aconductive material having a relatively higher work function value. Forexample, the first electrode 410 may be made of a transparent conductivematerial such as ITO, IZO or ZnO.

In one example, when the organic light emitting display device 300 is ofa top light emission type, a reflective electrode or a reflective layermay be further formed below the first electrode 410. For example, thereflective electrode or reflective layer may be made of any one ofaluminum (Al), silver (Ag), nickel (Ni), and aluminum-palladium-copper(APC alloy).

On the protective layer 370, a bank layer 380 covering an edge of thefirst electrode 410 is formed. The bank layer 380 exposes a centerregion of the first electrode 410 corresponding to the pixel region.

An organic light-emitting layer 430 is formed on the first electrode410. In one example, the organic light-emitting layer 430 may have atleast two light emission sub-stacks shown in FIG. 1 and FIG. 2.Accordingly, the organic electroluminescent device 400 may have a tandemstructure.

A second electrode 420 is formed on the organic light-emitting layer430. The second electrode 420 may be disposed over an entire displayregion and may be made of a conductive material having a relativelylower work function value and may act as a cathode. For example, thesecond electrode 420 may be made of any one of aluminum (Al), magnesium(Mg), and aluminum-magnesium alloy (AlMg).

The first electrode 410, the organic light-emitting layer 430 and thesecond electrode 420 together define the organic electroluminescentdevice 400.

On the second electrode 420, the encapsulation film 390 is formed toprevent external moisture from penetrating into the organicelectroluminescent device 400. Although not shown, the encapsulationfilm 390 may have a triple layer structure in which a first inorganiclayer and an organic layer and a second inorganic layer are sequentiallystacked. However, the present disclosure is not limited thereto.

As used herein, the term “halogen group” may include fluorine, chlorine,bromine or iodine.

As used herein, the term “alkyl” means a monovalent substituent derivedfrom straight or branched saturated hydrocarbons having 1 to 40 carbonatoms. Examples thereof include, but are not limited to, methyl, ethyl,propyl, isobutyl, sec-butyl, pentyl, iso-amyl and hexyl.

As used herein, the term “alkenyl” means a monovalent substituentderived from linear or branched unsaturated hydrocarbons having one ormore carbon-carbon double bonds and having 2 to 40 carbon atoms.Examples thereof include, but are not limited to, vinyl, allyl,isopropenyl, 2-butenyl, and the like.

As used herein, the term “alkynyl” means a monovalent substituentderived from linear or branched unsaturated hydrocarbons having one ormore carbon-carbon triple bonds and having 2 to 40 carbon atoms.Examples thereof include, but are not limited to, ethynyl, 2-propynyl,and the like.

As used herein, the term “aryl” means a monovalent substituent derivedfrom aromatic hydrocarbons having a single ring or a combination of twoor more rings and having 2 to 60 carbon atoms. Further, such aryl mayhave a form in which two or more rings are simply pendant with eachother or are condensed with each other. Examples of such aryl include,but are not limited to, phenyl, naphthyl, phenanthryl, anthryl,dimethylfluorenyl, and the like.

As used herein, the term “heteroaryl” means a monovalent substituentderived from monoheterocyclic or polyheterocyclic aromatic hydrocarbonshaving 6 to 30 carbon atoms. In this connection, at least one carbon,preferably 1 to 3 carbons in a ring is substituted with a heteroatomsuch as N, O, S or Se. Furthermore, such heteroaryl may have a form inwhich two or more rings are simply pendant with each other or arecondensed with each other or are condensed with the aryl group. Examplesof such heteroaryl include 6-membered monocyclic rings such as pyridyl,pyrazinyl, pyrimidinyl, pyridazinyl, and triazinyl, polycyclic ringssuch as phenoxathienyl, indolizinyl, indolyl, purinyl, quinolyl,benzothiazole, carbazolyl, and 2-furanyl, N-imidazolyl, 2-isoxazolyl,2-pyridinyl, 2-pyrimidinyl, etc. However, the present disclosure is notlimited thereto.

As used herein, the term “aryloxy” refers to a monovalent substituentrepresented by RO—, wherein R represents aryl having 6 to 60 carbonatoms. Examples of such aryloxy include, but are not limited to,phenyloxy, naphthyloxy, diphenyloxy, and the like.

As used herein, the term “alkyloxy” means a monovalent substituentrepresented by R′O—, where R′ means alkyl having 1 to 40 carbon atoms.Such alkyloxy has a linear, branched or cyclic structure. Examples ofalkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy,1-propoxy, t-butoxy, n-butoxy and pentoxy.

As used herein, the term “alkoxy” refers to a straight chain, branchedchain or cyclic chain. A carbon number of the alkoxy is not particularlylimited, but the alkoxy preferably has 1 to 20 carbon atoms. Specificexamples thereof include, but are not limited to, methoxy, ethoxy,n-propoxy, isopropoxy, i-propyloxy, n-butoxy, isobutoxy, tert-butoxy,sec-butoxy, n-pentyloxy, neopentyloxy, isopentyloxy, n-hexyloxy,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy,benzyloxy, p-methylbenzyloxy,

As used herein, the term “aralkyl” means an univalent radical derivedfrom an alkyl radical by replacing one or more hydrogen atoms with arylgroups. Preferred aralkyls includes lower alkyl groups. Non-limitingexamples of suitable aralkyl groups include benzyl, 2-phenethyl andnaphthalenylmethyl. A bond to a parent moiety is achieved via the alkyl.

As used herein, the term “arylamino group” means an amine substitutedwith an aryl group having 6 to 30 carbon atoms.

As used herein, the term “alkylamino group” means an amine substitutedwith an alkyl group having 1 to 30 carbon atoms.

As used herein, the term “aralkylamino group” means an amine substitutedwith an aryl-alkyl group having from 6 to 30 carbon atoms.

As used herein, the term “heteroarylamino group” means an amine groupsubstituted with an aryl group having 6 to 30 carbon atoms and aheterocyclic group.

As used herein, the term “heteroaralkyl group” means an aryl-alkyl groupsubstituted with a heterocyclic group.

As used herein, the term “cycloalkyl” means a monovalent substituentderived from monocyclic or polycyclic non-aromatic hydrocarbons having 3to 40 carbon atoms. Examples of such cycloalkyls include, but are notlimited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, norbornyl,adamantine, and the like.

As used herein, the term “heterocycloalkyl” means a monovalentsubstituent derived from non-aromatic hydrocarbon having 3 to 40 carbonatoms, where at least one carbon, preferably 1 to 3 carbons in a ring issubstituted with a heteroatom such as N, O, S or Se. Examples of suchheterocycloalkyl include, but are not limited to, morpholine,piperazine, and the like.

As used herein, the term “alkylsilyl” refers to silyl substituted withalkyl having 1 to 40 carbon atoms.

As used herein, the term “arylsilyl” means silyl substituted with arylhaving 6 to 60 carbon atoms.

As used herein, the term “condensed rings” means condensed aliphaticrings, condensed aromatic rings, condensed hetero-aliphatic rings,condensed hetero-aromatic rings, or combinations thereof.

As used herein, a term “a specific group bonds to an adjacent group toform a ring” means that the specific group bonds to the adjacent groupto form a substituted or unsubstituted aliphatic hydrocarbon ring; asubstituted or unsubstituted aromatic hydrocarbon ring; a substituted orunsubstituted aliphatic heterocycle; a substituted or unsubstitutedaromatic heterocycle; or condensed rings thereof.

As used herein, the term “aliphatic hydrocarbon ring” refers to a ringthat is not aromatic and consists only of carbon and hydrogen atoms.

As used herein, examples of the “aromatic hydrocarbon ring” include, butare not limited to, phenyl group, naphthyl group, anthracenyl group, andthe like.

As used herein, the term “aliphatic hetero ring” means an aliphatic ringcontaining one or more heteroatoms.

As used herein, the term “aromatic hetero ring” means an aromatic ringcontaining one or more heteroatoms.

As used herein, aliphatic hydrocarbon rings, aromatic hydrocarbon rings,aliphatic heterocyclic rings and aromatic heterocyclic rings may bemonocyclic or polycyclic.

As used herein, the term “substituted” means that a hydrogen atom bondedto a carbon atom in the compound is changed to another substituent. Aposition at which substitution occurs may refer to a position where thehydrogen atom is substituted. That is, the position is not limited to aspecific position as long as a substituent is able to substitute at theposition. When two or substitutions occur, two or more substituents maybe the same or different.

As used herein, the term “unsubstituted” means that a hydrogen atomreplaces another substituent. As used herein, the hydrogen atom mayinclude hydrogen, deuterium, and tritium.

In accordance with the present disclosure, the organicelectroluminescent device has the organic layer containing thedeuterated anthracene organic compound to realize the lowered drivingvoltage, the increased lifetime, and excellent luminescence efficiencyand external quantum efficiency (EQE) characteristics.

BRIEF DESCRIPTION OF THE SEVERAL VIEWS OF THE DRAWINGS

FIG. 1 shows a schematic cross-sectional view of an organicelectroluminescent device having a tandem structure having two lightemission sub-stacks and containing a compound represented by theChemical Formula 1 according to one embodiment of the presentdisclosure.

FIG. 2 shows a schematic cross-sectional view of an organicelectroluminescent device having a tandem structure having three lightemission sub-stacks and containing a compound represented by theChemical Formula 1 according to another embodiment of the presentdisclosure.

FIG. 3 is a cross-sectional view schematically showing an organic lightemission display device having an organic electroluminescent deviceaccording to still another embodiment of the present disclosure.

DETAILED DESCRIPTION

Embodiments of the present disclosure are provided to more fullydescribe the present disclosure to those skilled in the art. Thefollowing embodiments may be modified in various different forms. Ascope of the present disclosure is not limited to the followingembodiments. Rather, these embodiments are provided so that the presentdisclosure will be more thorough and complete and are provided to fullyconvey ideas of the present disclosure to those skilled in the art.

According to one preferred implementation of the present disclosure, thecompound represented by the Chemical Formula 1 may be selected from agroup consisting of following compounds, but are not limited thereto:

Hereinafter, methods for synthesizing the compounds represented by theChemical Formulas 1 and 2 will be described below as a representativeexample.

However, the methods for synthesizing the compounds in accordance withthe present disclosure is not limited to following exemplified methods.The compounds in accordance with the present disclosure may be preparedby methods illustrated below and

Synthesis Example 1: Synthesis of Compound 6

4-(10-bromoanthracene-9-yl)dibenzofuran-d8 (5.54 g, 10.0 mmol),(4-(naphthalen-1-yl)phenyl)boronic acid (2.73 g, 11.0 mmol), potassiumcarbonate (5.16 g, 20 mmol), 100 mL of toluene, 20 mL of water and 100mL of ethanol were mixed with each other.

Then, tetrakis(triphenylphosphine)palladium (0.231 g, 0.20 mmol) wasadded to the mixture which in turn was refluxed for 10 hours.Thereafter, the resulting mixture was cooled to a room temperature, andthen water was added thereto. A layer separation was performed to obtainan organic layer. The organic layer was treated with MgSO₄ to removemoisture therefrom.

After filtration of the organic layer, filtrate was concentrated under areduced pressure. The concentrate was subjected to column chromatographyusing dichloromethane and n-hexane as a developing solvent to obtain3.38 g (yield: 25%) of the present compound 6.

MS (MALDI-TOF) m/z: 554 [M]⁺

Synthesis Example 2: Synthesis of Compound 7

4-(10-bromoanthracene-9-yl)dibenzofuran-d8 (5.54 g, 10.0 mmol),(3-(naphthalen-1-yl)phenyl)boronic acid (2.73 g, 11.0 mmol), potassiumcarbonate (5.16 g, 20 mmol), 100 mL of toluene, 20 mL of water and 100mL of ethanol were mixed with each other.

Then, tetrakis(triphenylphosphine)palladium (0.231 g, 0.20 mmol) wasadded to the mixture which in turn was refluxed for 10 hours.Thereafter, the resulting mixture was cooled to a room temperature, andthen water was added thereto. A layer separation was performed to obtainan organic layer. The organic layer was treated with MgSO₄ to removemoisture therefrom.

After filtration of the organic layer, filtrate was concentrated under areduced pressure. The concentrate was subjected to column chromatographyusing dichloromethane and n-hexane as a developing solvent to obtain3.38 g (yield: 61%) of the present compound 7.

MS (MALDI-TOF) m/z: 554 [M]⁺

Synthesis Example 3: Synthesis of Compound 1

A starting material 1-A 3.92 g (10 mmol), a starting material 1-B 2.33 g(11 mmol), potassium carbonate (5.16 g, 20 mmol), 100 mL of toluene, 20mL of water and 100 mL of ethanol were mixed with each other.

Then, tetrakis(triphenylphosphine)palladium (0.231 g, 0.20 mmol) wasadded to the mixture which in turn was refluxed for 10 hours.Thereafter, the resulting mixture was cooled to a room temperature, andthen water was added thereto. A layer separation was performed to obtainan organic layer. The organic layer was treated with MgSO₄ to removemoisture therefrom.

After filtration of the organic layer, filtrate was concentrated under areduced pressure. The concentrate was subjected to column chromatographyusing dichloromethane and n-hexane as a developing solvent to obtain 1 g(yield: 62%) of the present compound 1.

MS (MALDI-TOF) m/z: 478 [M]⁺

Synthesis Example 4: Synthesis of Compound 3

2.7 g (yield 51%) of the present compound 3 was obtained using the samemanner as in Synthesis Example 1 except that 2.44 g (11 mmol) of astarting material 3-B was used instead of(4-(naphthalen-1-yl)phenyl)boronic acid.

MS (MALDI-TOF) m/z: 528 [M]⁺

Synthesis Example 5: Synthesis of Compound 5

3.66 g (yield 66%) of the present compound 5 was obtained using the samemanner as in Synthesis Example 1 except that 2.73 g (11 mmol) of astarting material 5-B was used instead of(4-(naphthalen-1-yl)phenyl)boronic acid.

MS (MALDI-TOF) m/z: 554 [M]⁺

Synthesis Example 6: Synthesis of Compound 9

3.5 g (yield 63%) of the present compound 9 was obtained using the samemanner as in Synthesis Example 1 except that 2.44 g (11 mmol) of astarting material 9-B was used instead of(4-(naphthalen-1-yl)phenyl)boronic acid.

Synthesis Example 7: Synthesis of Compound 10

3.5 g (yield 63%) of the present compound 10 was obtained using the samemanner as in Synthesis Example 1 except that 2.73 g (11 mmol) of astarting material 10-B was used instead of(4-(naphthalen-1-yl)phenyl)boronic acid.

Synthesis Example 8: Synthesis of Compound 13

3.32 g (yield 60%) of the present compound 13 was obtained using thesame manner as in Synthesis Example 3 except that a starting material13-B 3.17 g (11 mmol) was used instead of the starting material 1-B.

MS (MALDI-TOF) m/z: 554 [M]⁺

Synthesis Example 9: Synthesis of Compound 14

3.35 g (yield 64%) of the present compound 14 was obtained using thesame manner as in Synthesis Example 3 except that a starting material14-A 3.92 g (10 mmol) and a starting material 13-B 3.17 g (11 mmol) wereused instead of the starting materials 1-A and 1-B.

MS (MALDI-TOF) m/z: 554 [M]⁺

Synthesis Example 10: Synthesis of Compound 17

3.74 g (yield 62%) of the present compound 17 was obtained using thesame manner as in Synthesis Example 3 except that a starting material17-A 4.401 g (10 mmol) and a starting material 13-B 3.17 g (11 mmol)were used instead of the starting materials 1-A and 1-B.

MS (MALDI-TOF) m/z: 604 [M]⁺

Synthesis Example 11: Synthesis of Compound 21

2.86 g (yield 58%) of the present compound 21 was obtained using thesame manner as in Synthesis Example 3 except that a starting material21-A 3.98 g (10 mmol) and a starting material 21-B 2.4 g (11 mmol) wereused instead of the starting materials 1-A and 1-B.

MS (MALDI-TOF) m/z: 492 [M]⁺

Synthesis Example 12: Synthesis of Compound 22

2.98 g (yield 52%) of the present compound 22 was obtained using thesame manner as in Synthesis Example 3 except that a starting material22-A 4.78 g (10 mmol) and a starting material 21-B 2.4 g (11 mmol) wereused instead of the starting materials 1-A and 1-B.

MS (MALDI-TOF) m/z: 572 [M]⁺

Synthesis Example 13: Synthesis of Compound 36

2.86 g (yield 58%) of the present compound 36 was obtained using thesame manner as in Synthesis Example 3 except that a starting material36-A 3.98 g (10 mmol) and a starting material 36-B 2.4 g (11 mmol) wereused instead of the starting materials 1-A and 1-B.

MS (MALDI-TOF) m/z: 492 [M]⁺

Synthesis Example 14: Synthesis of Compound 39

2.98 g (yield 52%) of the present compound 39 was obtained using thesame manner as in Synthesis Example 3 except that a starting material39-A 4.78 g (10 mmol) and a starting material 39-B 2.4 g (11 mmol) wereused instead of the starting materials 1-A and 1-B.

MS (MALDI-TOF) m/z: 572 [M]⁺

Synthesis Example 15: Synthesis of Compound 44

3.66 g (yield 66%) of the present compound 44 was obtained using thesame manner as in Synthesis Example 3 except that a starting material44-A 4.30 g (10 mmol) and a starting material 5-B 2.73 g (11 mmol) wereused instead of the starting materials 1-A and 1-B.

MS (MALDI-TOF) m/z: 554 [M]⁺

Synthesis Example 16: Synthesis of Compound 72

3.06 g (yield 58%) of the present compound 72 was obtained using thesame manner as in Synthesis Example 3 except that a starting material14-A 3.91 g (10 mmol) and a starting material 72-B 2.88 g (11 mmol) wereused instead of the starting materials 1-A and 1-B.

MS (MALDI-TOF) m/z: 528 [M]⁺

Synthesis Example 17: Synthesis of Compound 73

2.77 g (yield 58%) of the present compound 73 was obtained using thesame manner as in Synthesis Example 3 except that a starting material73-A 3.41 g (10 mmol) and a starting material 72-B 2.88 g (11 mmol) wereused instead of the starting materials 1-A and 1-B.

MS (MALDI-TOF) m/z: 478 [M]⁺

Synthesis Example 18: Synthesis of Compound 79

3.66 g (yield 66%) of the present compound 79 was obtained using thesame manner as in Synthesis Example 3 except that a starting material79-A 4.16 g (10 mmol) and a starting material 79-B 2.88 g (11 mmol) wereused instead of the starting materials 1-A and 1-B.

MS (MALDI-TOF) m/z: 554 [M]⁺

Synthesis Example 19: Synthesis of Compound 108

2.83 g (yield 52%) of the present compound 108 was obtained using thesame manner as in Synthesis Example 3 except that a starting material108-A 3.45 g (10 mmol) and a starting material 108-B 3.55 g (11 mmol)were used instead of the starting materials 1-A and 1-B.

MS (MALDI-TOF) m/z: 57 [M]⁺

Synthesis Example 20: Synthesis of Compound 111

3.26 g (yield 66%) of the present compound 111 was obtained using thesame manner as in Synthesis Example 3 except that a starting material1-A 3.90 g (10 mmol) and a starting material 111-B 2.51 g (11 mmol) wereused instead of the starting materials 1-A and 1-B.

MS (MALDI-TOF) m/z: 494 [M]⁺

Synthesis Example 21: Synthesis of Compound 113

3.76 g (yield 66%) of the present compound 113 was obtained using thesame manner as in Synthesis Example 3 except that a starting material113-A 4.46 g (10 mmol) and a starting material 5-B 2.73 g (11 mmol) wereused instead of the starting materials 1-A and 1-B.

MS (MALDI-TOF) m/z: 570 [M]⁺

Synthesis Example 22: Synthesis of Compound 114

3.53 g (62% yield) of the present compound 114 was obtained in the samemanner as in Synthesis Example 2 except that 4.46 g (10 mmol) of astarting material 113-A was used instead of4-(10-bromoanthracene-9-yl)dibenzofuran-d8.

MS (MALDI-TOF) m/z: 570 [M]⁺

Synthesis Example 23: Synthesis of Compound 199

2.64 g (51% yield) of the present compound 199 was obtained using thesame manner as in Synthesis Example 1 except that 2.33 g (11 mmol) of astarting material 1-B was used instead of (4-(naphthalen-1-yl)phenyl)boron acid.

Synthesis Example 24: Synthesis of Compound 224

3.76 g (yield 66%) of the present compound 224 was obtained using thesame manner as in Synthesis Example 3 except that a starting material113-A 4.46 g (10 mmol) and a starting material 13-B 3.17 g (11 mmol)were used instead of the starting materials 1-A and 1-B.

MS (MALDI-TOF) m/z: 570 [M]⁺

Present Example 1: Manufacturing of Organic Electroluminescent Device

An Ag alloy layer as a light-reflecting layer, and an ITO (10 nm) layeras an anode of an organic electroluminescent device were sequentiallydeposited on a substrate. Then, patterning was performed using aphoto-lithograph process to divide the substrate region into cathode andanode regions and an insulating layer region. A UV ozone treatment and asurface-treatment using O₂:N₂ plasma were executed to enhance awork-function of the anode and to execute a descum process. Then, 1, 4,5, 8, 9, 11-hexaazatriphenylene-hexacarbonitrile (HAT-CN) as ahole-injecting layer (HIL) at 100-Å thickness was deposited on the ITOlayer.

Then, N4, N4, N4′,N4′-tetra([1,1′-biphenyl]-4-yl)-[1,1′-biphenyl]-4,4′-diamine was vacuumdeposited on the hole-injecting layer (HIL), to form a 1000-Å thickhole-transporting layer (HTL).

Then, on top of the hole-transporting layer (HTL), N-phenyl-N-(4-(spiro[benzo[de]anthracene-7,9-fluorene]-2-yl)phenyl)dibenzo[b,d]furan-4-amineas an electron-blocking layer (EBL) was deposited in a thickness of 150angstroms. Then, on top of the electron-blocking layer (EBL), thepresent compound 6 as a host material of a light-emitting layer (EML)was deposited. At the same time, N1, N1, N6,N6-tetrakis(4-(1-silyl)phenyl)pyrene-1,6-diamine as dopants was dopedinto the host material, to from the light emitting layer (EML).

Then, a mixture of2-(4-(9,10-di(naphthalene-2-yl)anthracene-2-yl)phenyl)-1-phenyl-1H-benzo[d]imidazoleand LiQ in a weight ratio of 1:1 was deposited to a thickness of 360 Åas an electron-transporting layer (ETL) on the EML layer. Then, amixture of magnesium (Mg) and silver (Ag) at a ratio of 9:1 wasdeposited as a cathode at a thickness of 160 Å on the ETL layer.

Next, N4, N4′-diphenyl-N4,N4′-bis(4-(9-phenyl-9H-carbazol-3-yl)phenyl-[1, 1′-biphenyl]-4,4′-diamine was deposited as a capping layer (CPL) to a thickness of 63to 65 nm on the cathode layer.

Then, we attached a seal cap to the capping layer (CPL) with a UV curingadhesive to protect the organic electroluminescent device fromatmospheric O₂ or moisture. In this way, the organic electroluminescentdevice was fabricated.

Present Example 2 to 11: Manufacturing of Organic ElectroluminescentDevice

Organic electroluminescent devices were fabricated in the same manner asin Present Example 1 except that the present compounds 1, 3, 5, 9, 10,13, 14, 17, 21 and 22 of a following Table 1 were used as the hostmaterial instead of the compound 6.

Present Example 12: Manufacturing of Organic Electroluminescent Device

An Ag alloy layer as a light-reflecting layer, and an ITO (10 nm) layeras an anode of an organic electroluminescent device were sequentiallydeposited on a substrate. Then, patterning was performed using aphoto-lithograph process to divide the substrate region into cathode andanode regions and an insulating layer region. A UV ozone treatment and asurface-treatment using O₂:N₂ plasma were executed to enhance awork-function of the anode and to execute a descum process. Then, 1, 4,5, 8, 9, 11-hexaazatriphenylene-hexacarbonitrile (HAT-CN) as ahole-injecting layer (HIL) at 100-Å thickness was deposited on the ITOlayer.

Then, N4, N4, N4′,N4′-tetra([1,1′-biphenyl]-4-yl)-[1,1′-biphenyl]-4,4′-diamine was vacuumdeposited on the hole-injecting layer (HIL), to form a 1000-Å thickhole-transporting layer (HTL).

Then, on top of the hole-transporting layer (HTL), N-phenyl-N-(4-(spiro[benzo[de]anthracene-7,9-fluorene]-2-yl)phenyl)dibenzo[b,d]furan-4-amineas an electron-blocking layer (EBL) was deposited in a thickness of 150angstroms. Then, on top of the electron-blocking layer (EBL), thepresent compound 36 as a host material of a light-emitting layer (EML)was deposited. At the same time, a following compound 1-B as dopants wasdoped into the host material, to from the light emitting layer (EML).

Compound 1-B

Then, a mixture of2-(4-(9,10-di(naphthalene-2-yl)anthracene-2-yl)phenyl)-1-phenyl-1H-benzo[d]imidazoleand LiQ in a weight ratio of 1:1 was deposited to a thickness of 360 Åas an electron-transporting layer (ETL) on the EML layer. Then, amixture of magnesium (Mg) and silver (Ag) at a ratio of 9:1 wasdeposited as a cathode at a thickness of 160 Å on the ETL layer.

Next, N4, N4′-diphenyl-N4,N4′-bis(4-(9-phenyl-9H-carbazol-3-yl)phenyl-[1,1′-biphenyl]-4,4′-diamine was deposited as a capping layer (CPL) to a thickness of 63to 65 nm on the cathode layer.

Then, we attached a seal cap to the capping layer (CPL) with a UV curingadhesive to protect the organic electroluminescent device fromatmospheric O₂ or moisture. In this way, the organic electroluminescentdevice was fabricated.

Present Example 13 to 22: Organic Electroluminescent Device

Organic electroluminescent devices were fabricated using the same methodas in the Present Example 12 except that the present compounds 39, 44,79, 72, 73, 108, 111, 113, 199, 224 of the following Table 1 were usedas the host material instead of the compound 36.

Comparative Examples 1 to 7: Manufacturing of Organic ElectroluminescentDevice

Comparative organic electroluminescent devices were fabricated using thesame method as in the Present Example 1 except that followingComparative Compounds A to J were employed as the host material insteadof the compound 6.

Experimental Example 1: Property Analysis of Organic ElectroluminescentDevice

For the organic electroluminescent devices as prepared according toPresent Examples 1 to 22 and Comparative Examples 1 to 9, drivingvoltages and luminous efficiencies characteristics in driving thedevices at 10 mA/cm² current and lifespan characteristics atacceleration of the devices at 20 mA/cm² were analyzed. Results areshown in the following Table 1.

“T95 lifespan” in Table 1 below refers to a time duration which it takesfor a display device to lose 5% of its initial brightness. The T95lifespan is a customer requirement that is the most difficult to meet.Thus, the T95 lifespan determines whether a image burn in occurs in thedisplay device.

TABLE 1 External Current Power quantum Color Lifespan Voltage efficiencyefficiency efficiency coordinate T95 Examples Host (v) (Cd/A) (lm/w)EQE(%) CIEx CIEy (hrs) Comparative Comparative 3.78 5.3 4.7 11.4 0.1420.048 92 Example 1 Compound A Comparative Comparative 3.81 5.7 4.7 11.30.141 0.050 100 Example 2 Compound B Comparative Comparative 3.82 5.84.8 11.6 0.141 0.049 105 Example 3 Compound C Comparative Comparative4.2 5.6 4.2 10.9 0.139 0.052 120 Example 7 Compound G ComparativeComparative 4.15 5.4 4.1 10 0.138 0.054 100 Example 8 Compound HComparative Comparative 3.79 5.1 4.2 9.9 0.139 0.051 75 Example 9Compound I Present Compound 6 3.88 6.0 4.9 11.3 0.139 0.052 130 Example1 Present Compound 1 3.93 4.8 3.9 9.1 0.140 0.052 112 Example 2 PresentCompound 3 3.97 5.4 4.3 10.4 0.140 0.052 110 Example 3 Present Compound5 4.09 5.2 4.0 10.2 0.141 0.05 125 Example 4 Present Compound 9 3.87 4.73.8 8.8 0.139 0.053 120 Example 5 Present Compound 3.81 5.1 4.2 10.00.140 0.049 130 Example 6 10 Present Compound 3.91 5.0 4.0 9.4 0.1400.051 130 Example 7 13 Present Compound 4.0 4.8 3.8 9.3 0.141 0.048 135Example 8 14 Present Compound 4.1 5.2 4.2 10 0.139 0.052 110 Example 917 Present Compound 3.95 4.8 3.8 9.1 0.140 0.052 120 Example 10 21Present Compound 4.05 4.0 5.2 10.2 0.141 0.050 122 Example 11 22 PresentCompound 3.94 5.1 4.1 9.9 0.14 0.05 120 Example 12 36 (Boron D) PresentCompound 3.94 4.9 3.9 10.5 0.144 0.044 120 Example 13 39 (Boron D)Present Compound 3.94 4.9 3.9 10.5 0.144 0.044 120 Example 14 44 (BoronD) Present Compound 3.68 5.2 4.4 9.7 0.138 0.053 115 Example 15 79(Boron D) Present Compound 3.83 5.6 4.6 10.0 0.14 0.051 110 Example 1672 (Boron D) Present Compound 3.79 5.1 4.2 10.2 0.141 0.05 110 Example17 73 (Boron D) Present Compound 3.66 4.8 4.1 9.2 0.140 0.051 113Example 18 108 (Boron D) Present Compound 3.98 5.1 4.1 9.8 0.140 0.050119 Example 19 111 (Boron D) Present Compound 3.95 5.2 4.1 8.8 0.1390.051 120 Example 20 113 (Boron D) Present Compound 3.69 5.1 4.3 9.20.138 0.052 120 Example 21 199 (Boron D) Present Compound 3.75 5.1 4.110 0.140 0.050 125 Example 22 224 (Boron D)

As Table 1 shows, Present Example 1 which employs the compound accordingto the present disclosure as a host material exhibited excellent currentefficiency and lifespan increase up to about 47% compared to ComparativeExamples 1 to 3 which has a similar compound structure thereto. Further,Present Examples 1 to 22 in accordance with the present disclosure inwhich polar molecules are bonded to anthracene were found to have lowerdrive voltage than Comparative Examples 7 to 8 in which polar moleculeswere not bonded thereto.

From those findings, it may be concluded that the anthracene compound inaccordance with the present disclosure achieves lower drive voltage thanthat achieved by a host material with no polarity, and the deuterationleads to the longer lifespan.

Thus, it may be confirmed that the compounds represented by the ChemicalFormula 1 of the present disclosure contain polar molecules such asdibenzo furan or dibenzo thiophene, and the anthracene deuteration leadsto excellent properties such as the low drive voltage implementation andlong lifespan.

Present Examples 23 to 24: Manufacturing of Organic ElectroluminescentDevice

Organic electroluminescent devices were fabricated in the same manner asin Present Example 1, except that the compounds 7 or 114 of a followingTable 2 were used as the host material instead of the compound 6.

Experimental Example 2: Property Analysis of Organic ElectroluminescentDevice

For the organic electroluminescent devices as prepared according toPresent Examples 23 to 24 and Comparative Examples 4 to 8 and 10,driving voltages and luminous efficiencies characteristics in drivingthe devices at 10 mA/cm² current and lifespan characteristics atacceleration of the devices at 20 mA/cm² were analyzed. Results areshown in the following Table 2.

“T95 lifespan” in Table 2 below refers to a time duration which it takesfor a display device to lose 5% of its initial brightness. The T95lifespan is a customer requirement that is the most difficult to meet.Thus, the T95 lifespan determines whether a image burn in occurs in thedisplay device.

TABLE 2 External Current Power quantum Color Lifespan Voltage efficiencyefficiency efficiency coordinate T95 Examples Host (v) (Cd/A) (lm/w)EQE(%) CIEx CIEy (hrs) Comparative Comparative 4.13 5.9 4.5 11.0 0.1390.053 90 Example 4 Compound D Comparative Comparative 4.12 6.1 4.6 11.30.139 0.053 125 Example 5 Compound E Comparative Comparative 4.10 5.64.3 10.9 0.141 0.050 130 Example 6 Compound F Comparative Comparative4.24 5.6 4.1 10.9 0.139 0.052 120 Example 7 Compound G ComparativeComparative 4.19 5.4 4.1 10 0.138 0.054 100 Example 8 Compound H PresentCompound 7 4.12 6.1 4.6 11.3 0.139 0.053 160 Example 23 ComparativeComparative 4.05 5.7 4.4 11.6 0.142 0.046 95 Example 10 Compound JPresent Compound 3.97 5.9 4.7 8.8 0.139 0.053 120 Example 24 114

As Table 2 shows, Present Example 23 which employs the compoundaccording to the present disclosure as a host material exhibitedexcellent current efficiency and lifespan increase up to about 78%compared to Comparative Examples 4 to 6 which has a similar compoundstructure thereto.

As Table 2 shows, Present Example 24 which employs the compoundaccording to the present disclosure as a host material exhibitedexcellent current efficiency and lifespan increase up to about 23%compared to Comparative Example 10 which has a similar compoundstructure thereto.

Further, Present Examples 23 and 24 in accordance with the presentdisclosure in which polar molecules are bonded to anthracene were foundto have lower drive voltage than Comparative Examples 7 to 8 in whichpolar molecules were not bonded thereto.

Thus, it may be confirmed that the compounds represented by the ChemicalFormula 1 of the present disclosure contain polar molecules such asdibenzo furan or dibenzo thiophene, and the anthracene deuteration leadsto excellent properties such as the low drive voltage implementation andlong lifespan.

The description of the disclosed embodiments is provided to enable anyperson skilled in the art to make or use the present disclosure. Variousmodifications to these embodiments will be readily apparent to thoseskilled in the art of the present disclosure. The generic principlesdefined herein may be applied to other embodiments without departingfrom the scope of the present disclosure. Thus, the present disclosureis not to be construed as limited to the embodiments set forth herein,but is to be accorded the widest scope consistent with the principlesand novel features set forth herein.

The various embodiments described above can be combined to providefurther embodiments. All of the U.S. patents, U.S. patent applicationpublications, U.S. patent applications, foreign patents, foreign patentapplications and non-patent publications referred to in thisspecification and/or listed in the Application Data Sheet areincorporated herein by reference, in their entirety. Aspects of theembodiments can be modified, if necessary to employ concepts of thevarious patents, applications and publications to provide yet furtherembodiments.

These and other changes can be made to the embodiments in light of theabove-detailed description. In general, in the following claims, theterms used should not be construed to limit the claims to the specificembodiments disclosed in the specification and the claims, but should beconstrued to include all possible embodiments along with the full scopeof equivalents to which such claims are entitled. Accordingly, theclaims are not limited by the disclosure.

1. A compound represented by a following Chemical Formula 1:

wherein Y denotes a substituent represented by a following ChemicalFormula 2:

wherein X is O or S, n is an integer of 0 to 4, m is an integer of 0 to3, wherein L₁ and L₂ are the same or different from each other, and eachof L₁ and L₂ independently are selected from a group consisting of adirect bond, a substituted or unsubstituted arylene group having 6 to 30carbon atoms, a substituted or unsubstituted heteroarylene group having6 to 30 ring constituting atoms, a substituted or unsubstituted alkylenegroup having 2 to 10 carbon atoms, a substituted or unsubstitutedcycloalkylene group having 2 to 10 carbon atoms, a substituted orunsubstituted alkenylene group having 2 to 10 carbon atoms, asubstituted or unsubstituted cycloalkenylene group having 2 to 10 carbonatoms, a substituted or unsubstituted heteroalkylene group having 2 to10 carbon atoms, a substituted or unsubstituted heterocycloalkylenegroup having 2 to 10 carbon atoms, a substituted or unsubstitutedheteroalkenylene group having 2 to 10 carbon atoms, and a substituted orunsubstituted heterocycloalkenylene group having 2 to 10 carbon atoms,wherein Ar₁ is selected from a group consisting of a substituted orunsubstituted aryl group having 6 to 30 carbon atoms, a substituted orunsubstituted heteroaryl group having 3 to 30 carbon atoms, asubstituted or unsubstituted alkyl group having 1 to 20 carbon atoms, asubstituted or unsubstituted cycloalkyl group having 1 to 20 carbonatoms, a substituted or unsubstituted heteroalkyl group having 1 to 20carbon atoms, a substituted or unsubstituted heterocycloalkyl grouphaving 1 to 20 carbon atoms, a substituted or unsubstituted alkenylgroup having 1 to 20 carbon atoms, a substituted or unsubstitutedcycloalkenyl group having 1 to 20 carbon atoms, and a substituted orunsubstituted heteroalkenyl group having 1 to 20 carbon atoms, whereinR₁, R₂, R₃, R₄, R₅, R₆, R₇, R₈, R₉, and R₁₀ are, at each occurrence,independently selected from a group consisting of hydrogen, deuterium, asubstituted or unsubstituted alkyl group having 1 to 30 carbon atoms, asubstituted or unsubstituted cycloalkyl group having 3 to 30 carbonatoms, a substituted or unsubstituted alkenyl group having 2 to 30carbon atoms, a substituted or unsubstituted alkynyl group having 2 to24 carbon atoms, a substituted or unsubstituted heteroalkyl group having2 to 30 carbon atoms, a substituted or unsubstituted aralkyl grouphaving 7 to 30 carbon atoms, a substituted or unsubstituted aryl grouphaving 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylgroup having 2 to 30 carbon atoms, and a substituted or unsubstitutedheteroarylalkyl group having 3 to 30 carbon atoms, or wherein eachoccurrence of R₉ may, together with the carbon to which it is attached,join with an adjacent R₉ to form a ring, or wherein each occurrence ofR₁₀ may, together with the carbon to which it is attached, join with anadjacent R₁₀ to form a ring, wherein each of R₁, R₂, R₃, R₄, R₅, R₆, R₇,R₈, R₉, R₁₀, L₁, L₂, and Ar₁ is independently substituted with at leastone substituent selected from a group consisting of hydrogen, deuterium,a cyano group, a nitro group, a halogen group, a hydroxy group, asubstituted or unsubstituted alkyl having 1 to 30 carbon atoms, asubstituted or unsubstituted cycloalkyl group having 3 to 30 carbonatoms, a substituted or unsubstituted alkenyl group having 2 to 30carbon atoms, a substituted or unsubstituted alkynyl group having 2 to24 carbon atoms, a substituted or unsubstituted heteroalkyl group having2 to 30 carbon atoms, a substituted or unsubstituted aralkyl grouphaving 7 to 30 carbon atoms, a substituted or unsubstituted aryl grouphaving 6 to 30 carbon atoms, a substituted or a heteroaryl group having2 to 30 carbon atoms, a substituted or unsubstituted heteroarylalkylgroup having 3 to 30 carbon atoms, a substituted or unsubstituted alkoxygroup having 1 to 30 carbon atoms, a substituted or unsubstitutedalkylamino group having 1 to 30 carbon atoms, a substituted orunsubstituted arylamino group having 6 to 30 carbon atoms, a substitutedor unsubstituted aralkylamino group having 6 to 30 carbon atoms, asubstituted or unsubstituted heteroarylamino group having 2 to 24 carbonatoms, a substituted or unsubstituted alkylsilyl group having 1 to 30carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to30 carbon atoms, and a substituted or unsubstituted aryloxy group having6 to 30 carbon atoms, and wherein at least one of L₁, L₂, Ar₁, R₁, R₂,R₃, R₄, R₅, R₆, R₇, R₈, R₉, or R₁₀ includes deuterium.
 2. The compoundof claim 1, wherein at least one of R₁, R₂, R₃, R₄, R₅, R₆, R₇, or R₈includes deuterium.
 3. The compound of claim 1, wherein L₁ is selectedfrom a group consisting of a direct bond, a substituted or unsubstitutedarylene group having 6 to 30 carbon atoms, and a substituted orunsubstituted heteroarylene group having 6 to 30 ring constitutingatoms, and wherein L₂ is a direct bond or a substituted or unsubstitutedphenylene group.
 4. The compound of claim 1, wherein the compoundrepresented by the Chemical Formula 1 is selected from a groupconsisting of:


5. An organic electroluminescent device, comprising: a first electrode;a second electrode facing away the first electrode; and at least oneorganic layer interposed between the first electrode and the secondelectrode, wherein the at least one organic layer contains at least onecompound having the Chemical Formula 1 of claim
 1. 6. The organicelectroluminescent device of claim 5, wherein the organic layer definesone selected from a group consisting of a hole-injecting layer, ahole-transporting layer, a light-emitting layer, a hole-blocking layer,an electron-transporting layer and an electron-injecting layer.
 7. Theorganic electroluminescent device of claim 5, wherein the organic layerdefines a light-emitting layer, wherein the light-emitting layercontains the compound of the Chemical Formula 1 as a host material. 8.An organic electroluminescent device, comprising: a first light emissionsub-stack for rendering first color light; and a second light emissionsub-stack stacked on the first light emission sub-stack, wherein thesecond light emission sub-stack renders second color light, wherein atleast one of the first light emission sub-stack and the second lightemission sub-stack contains a host material, wherein the host materialincludes a compound represented by a following Chemical Formula 1:

wherein Y denotes a substituent represented by a following ChemicalFormula 2:

wherein X is O or S, n is an integer of 0 to 4, m is an integer of 0 to3, wherein L₁ and L₂ are the same or different from each other, and eachof L₁ and L₂ independently are selected from a group consisting of adirect bond, a substituted or unsubstituted arylene group having 6 to 30carbon atoms, a substituted or unsubstituted heteroarylene group having6 to 30 ring constituting atoms, a substituted or unsubstituted alkylenegroup having 2 to 10 carbon atoms, a substituted or unsubstitutedcycloalkylene group having 2 to 10 carbon atoms, a substituted orunsubstituted alkenylene group having 2 to 10 carbon atoms, asubstituted or unsubstituted cycloalkenylene group having 2 to 10 carbonatoms, a substituted or unsubstituted heteroalkylene group having 2 to10 carbon atoms, a substituted or unsubstituted heterocycloalkylenegroup having 2 to 10 carbon atoms, a substituted or unsubstitutedheteroalkenylene group having 2 to 10 carbon atoms, and a substituted orunsubstituted heterocycloalkenylene group having 2 to 10 carbon atoms,wherein Ar₁ is selected from a group consisting of a substituted orunsubstituted aryl group having 6 to 30 carbon atoms, a substituted orunsubstituted heteroaryl group having 3 to 30 carbon atoms, asubstituted or unsubstituted alkyl group having 1 to 20 carbon atoms, asubstituted or unsubstituted cycloalkyl group having 1 to 20 carbonatoms, a substituted or unsubstituted heteroalkyl group having 1 to 20carbon atoms, a substituted or unsubstituted heterocycloalkyl grouphaving 1 to 20 carbon atoms, a substituted or unsubstituted alkenylgroup having 1 to 20 carbon atoms, a substituted or unsubstitutedcycloalkenyl group having 1 to 20 carbon atoms, and a substituted orunsubstituted heteroalkenyl group having 1 to 20 carbon atoms, whereinR₁, R₂, R₃, R₄, R₅, R₆, R₇, R₈, R₉, and R₁₀ are, at each occurrence,independently selected from a group consisting of hydrogen, deuterium, asubstituted or unsubstituted alkyl group having 1 to 30 carbon atoms, asubstituted or unsubstituted cycloalkyl group having 3 to 30 carbonatoms, a substituted or unsubstituted alkenyl group having 2 to 30carbon atoms, a substituted or unsubstituted alkynyl group having 2 to24 carbon atoms, a substituted or unsubstituted heteroalkyl group having2 to 30 carbon atoms, a substituted or unsubstituted aralkyl grouphaving 7 to 30 carbon atoms, a substituted or unsubstituted aryl grouphaving 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylgroup having 2 to 30 carbon atoms, and a substituted or unsubstitutedheteroarylalkyl group having 3 to 30 carbon atoms, or wherein eachoccurrence of R₉ may, together with the carbon to which it is attached,join with an adjacent R₉ to form a ring, or wherein each occurrence ofR₁₀ may, together with the carbon to which it is attached, join with anadjacent R₁₀ to form a ring, wherein each of R₁, R₂, R₃, R₄, R₅, R₆, R₇,R₈, R₉, R₁₀, L₁, L₂, and Ar₁ is independently substituted with at leastone substituent selected from a group consisting of hydrogen, deuterium,a cyano group, a nitro group, a halogen group, a hydroxy group, asubstituted or unsubstituted alkyl having 1 to 30 carbon atoms, asubstituted or unsubstituted cycloalkyl group having 3 to 30 carbonatoms, a substituted or unsubstituted alkenyl group having 2 to 30carbon atoms, a substituted or unsubstituted alkynyl group having 2 to24 carbon atoms, a substituted or unsubstituted heteroalkyl group having2 to 30 carbon atoms, a substituted or unsubstituted aralkyl grouphaving 7 to 30 carbon atoms, a substituted or unsubstituted aryl grouphaving 6 to 30 carbon atoms, a substituted or a heteroaryl group having2 to 30 carbon atoms, a substituted or unsubstituted heteroarylalkylgroup having 3 to 30 carbon atoms, a substituted or unsubstituted alkoxygroup having 1 to 30 carbon atoms, a substituted or unsubstitutedalkylamino group having 1 to 30 carbon atoms, a substituted orunsubstituted arylamino group having 6 to 30 carbon atoms, a substitutedor unsubstituted aralkylamino group having 6 to 30 carbon atoms, asubstituted or unsubstituted heteroarylamino group having 2 to 24 carbonatoms, a substituted or unsubstituted alkylsilyl group having 1 to 30carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to30 carbon atoms, and a substituted or unsubstituted aryloxy group having6 to 30 carbon atoms, and wherein at least one of L₁, L₂, Ar₁, R₁, R₂,R₃, R₄, R₅, R₆, R₇, R₈, R₉, or R₁₀ includes deuterium.
 9. The organicelectroluminescent device of claim 8, wherein at least one of R₁, R₂,R₃, R₄, R₅, R₆, R₇, or R₈ includes deuterium.
 10. The organicelectroluminescent device of claim 8, wherein L₁ is selected from agroup consisting of a direct bond, a substituted or unsubstitutedarylene group having 6 to 30 carbon atoms, and a substituted orunsubstituted heteroarylene group having 6 to 30 ring constitutingatoms, wherein L₂ is a direct bond or a substituted or unsubstitutedphenylene group.
 11. The organic electroluminescent device of claim 8,wherein the compound represented by the Chemical Formula 1 is selectedfrom a group consisting of:


12. The organic electroluminescent device of claim 8, wherein the firstlight emission sub-stack includes a first light-emitting layer, whereinthe second light emission sub-stack includes a second light-emittinglayer, and wherein at least one of the first light-emitting layer andthe second light-emitting layer contains the host material.
 13. Theorganic electroluminescent device of claim 8, wherein the first lightemission sub-stack includes a vertical sequential stack of a firstelectrode, a first hole-transporting layer, a first light-emitting layerand a first electron-transporting layer, wherein the second lightemission sub-stack includes a vertical sequential stack of a secondhole-transporting layer, a second light-emitting layer and a secondelectron-transporting layer, and wherein at least one of the firstlight-emitting layer and the second light-emitting layer contains thehost material.